4767. Hydrastine

Nomenclature

CAS number: 118-08-1
(3S)-6,7-Dimethoxy-3-[(5R)-5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl]-1(3H)-isobenzofuranone; l-β-hydrastine.
C21H21NO6; mol wt 383.39.
C 65.79%, H 5.52%, N 3.65%, O 25.04%.

Description and references

Isoln of naturally occurring l-β-form from Hydrastis canadensis L., Ranunculaceae together with berberine and canadine. Synthesis of diastereoisomeric mixtures of hydrastines: Hope et al., J. Chem. Soc. 1931, 236; Marshall et al., ibid. 1934, 1315; M. Hanaoka et al., Chem. Pharm. Bull. 27, 1947 (1979); J. R. Falck, S. Manna, Tetrahedron Lett. 22, 619 (1981). Resolution to the l-β-form: Haworth, Pinder, J. Chem. Soc. 1950, 1776; Haworth et al., Nature 165, 529 (1950). Structure: Knabe, Arch. Pharm. 293, 121 (1960). Abs config: Ohta et al., Tetrahedron Lett. 1963, 859; Blaha et al., Collect. Czech. Chem. Commun. 29, 2328 (1964); Snatzke et al., Tetrahedron 25, 5059 (1969). Biosynthesis: Gear, Spenser, Can. J. Chem. 41, 783 (1963).

Chemical structure

Properties

Orthorhombic prisms from alc, mp 132°. [α]D20 50° (c = 0.3 in abs alc). uv max (ethanol): 202, 218, 238, 298, 316 nm (log ε 4.79, 4.53, 4.15, 3.86, 3.63). pK 7.8. Freely sol in acetone and benzene; insol in water. The salts hydrolyze easily and do not crystallize well.

Derivative

Hydrochloride.

Nomenclature

CAS number: 5936-28-7
C21H21NO6.HCl; mol wt 419.86.
C 60.07%, H 5.28%, N 3.34%, O 22.86%, Cl 8.44%.

Description and references

Prepn: R. Paech, M. V. Tracy, Modern Methods of Plant Analysis vol. IV (Springer-Verlag, Berlin, 1955) p 383.

Properties

Powder, mp 116°. [α]D17 +127° (c = 4 in dil HCl). Very sol in water, alcohol; slightly sol in CHCl3; very slightly in ether. pH (0.5% aq soln): 4.2. Hygroscopic. Keep well closed.

Therapeutic Category

Hydrochloride formerly as uterine hemostatic, antiseptic.

Keywords

Antiseptic/Disinfectant; Quinolines